KR19980064777A - Foamable organosiloxane compositions curable with silicone foams with improved adhesion - Google Patents
Foamable organosiloxane compositions curable with silicone foams with improved adhesion Download PDFInfo
- Publication number
- KR19980064777A KR19980064777A KR1019970076170A KR19970076170A KR19980064777A KR 19980064777 A KR19980064777 A KR 19980064777A KR 1019970076170 A KR1019970076170 A KR 1019970076170A KR 19970076170 A KR19970076170 A KR 19970076170A KR 19980064777 A KR19980064777 A KR 19980064777A
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- KR
- South Korea
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- weight
- parts
- component
- silicon
- per molecule
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- 239000000203 mixture Substances 0.000 title claims abstract description 82
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 13
- 229920002323 Silicone foam Polymers 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 150000003755 zirconium compounds Chemical class 0.000 claims abstract description 14
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 239000006260 foam Substances 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 14
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000013514 silicone foam Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 abstract description 15
- 229910052697 platinum Inorganic materials 0.000 abstract description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 6
- -1 platinum group metals Chemical class 0.000 description 60
- 230000000052 comparative effect Effects 0.000 description 35
- 229920001577 copolymer Polymers 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 229920003023 plastic Polymers 0.000 description 13
- 239000004033 plastic Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 11
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 6
- 229910004298 SiO 2 Chemical group 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 4
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 229920001870 copolymer plastic Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 239000012764 mineral filler Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- CSJKPFQJIDMSGF-UHFFFAOYSA-K aluminum;tribenzoate Chemical compound [Al+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 CSJKPFQJIDMSGF-UHFFFAOYSA-K 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003060 catalysis inhibitor Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/142—Compounds containing oxygen but no halogen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/02—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by the reacting monomers or modifying agents during the preparation or modification of macromolecules
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- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/54—Silicon-containing compounds
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
Abstract
본 발명은 알케닐-작용성 폴리오가노실록산, 오가노하이드로겐실록산, 발포제, 백금 촉매 및 에폭시-작용성 화합물, 하이드록실-작용성 화합물, 테트라알킬오르토실리케이트, 오가노티타네이트와 알루미늄 또는 지르코늄 화합물을 포함하는 접착 촉진제를 포함하는 발포성의 경화가능한 오가노실록산 조성물에 관한 것이다.The present invention relates to alkenyl-functional polyorganosiloxanes, organohydrogensiloxanes, blowing agents, platinum catalysts and epoxy-functional compounds, hydroxyl-functional compounds, tetraalkylorthosilicates, organotitanates and aluminum or zirconium compounds. A foamable curable organosiloxane composition comprising an adhesion promoter comprising a.
Description
본 발명은 경화시 접착성이 향상된 실리콘 발포체를 생성하는 접착 촉진제를 함유하는 발포성 오가노실록산 조성물에 관한 것이다.The present invention relates to foamable organosiloxane compositions containing adhesion promoters that produce silicone foams having improved adhesion upon curing.
발포제로서 경화가능한 액체 폴리오가노실록산, 오가노하이드로겐실록산, 하이드록실-함유 화합물 및 백금족 금속 또는 이의 화합물과 경화 촉매를 포함하는 발포성 조성물은 미국 특허 제3,923,705호, 제4,026,843호, 제4,189,545호, 제4,590,222호, 제4,599,357호 및 제5,252,627호에 기술되어 있다.Foamable compositions comprising curable liquid polyorganosiloxanes, organohydrogensiloxanes, hydroxyl-containing compounds and platinum group metals or compounds thereof and curing catalysts as blowing agents are disclosed in US Pat. Nos. 3,923,705, 4,026,843, 4,189,545, 4,590,222, 4,599,357 and 5,252,627.
미국 특허 제5,595,826호는 알케닐-작용성 오가노폴리실록산, 오가노하이드로겐실록산, 에폭시-직용성 화합물, 하이드록실 그룹과 수소화규소를 갖는 화합물, 알케닐 또는 아실 그룹 및 알루미늄 또는 지르코늄 화합물을 포함하는 오가노실록산 조성물을 교시하고 있다.U.S. Patent 5,595,826 discloses alkenyl-functional organopolysiloxanes, organohydrogensiloxanes, epoxy-compatible compounds, compounds having hydroxyl groups and silicon hydrides, alkenyl or acyl groups, and aluminum or zirconium compounds Organosiloxane compositions are taught.
본 발명은 경화시, 플라스틱을 포함하는 각종 기판에 대한 접착성이 향상된 실리콘 발포체를 생성하는 발포성의, 경화가능한 오가노실록산 조성물을 제공한다. 본 발명의 오가노실록산 조성물은 분자당 평균 2개 이상의 알케닐 라디칼, 분자당 평균 2개 이상의 규소-결합된 수소 원자를 갖는 오가노하이드로겐실록산, 발포제, 백금 촉매 및 접착 촉진제를 함유하는 폴리오가노실록산을 포함한다. 접착 촉진제는 에폭시-작용성 화합물; 하나 이상의 하이드록시 그룹과 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 화합물; 테트라알킬오르토실리케이트; 오가노티타네이트 및 알루미늄 화합물 또는 지르코늄 화합물을 포함하는 화합물을 포함한다.The present invention provides a foamable, curable organosiloxane composition that, upon curing, produces silicone foams with improved adhesion to various substrates, including plastics. The organosiloxane composition of the present invention is a polyorgano containing an organohydrogensiloxane having an average of two or more alkenyl radicals per molecule, an average of two or more silicon-bonded hydrogen atoms per molecule, a blowing agent, a platinum catalyst and an adhesion promoter. Siloxanes. Adhesion promoters include epoxy-functional compounds; Compounds comprising at least one alkenyl group in the same molecule as at least one hydroxy group; Tetraalkylorthosilicates; Compounds including organotitanate and aluminum compounds or zirconium compounds.
본 발명은 또한 분자당 평균 2개 이상의 알케닐 라디칼을 함유하는 폴리오가노실록산, 분자당 평균 2개 이상의 규소-결합된 수소를 갖는 오가노하이드로겐실록산, 발포제, 백금 촉매, 및 에폭시-작용성 화합물; 하나 이상의 하이드록시 그룹과 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 화합물; 테트라알킬오르토실리케이트; 오가노티타네이트 및 알루미늄 화합물 또는 지르코늄 화합물을 포함하는 접착 촉진제를 포함하는 발포-형성 조성물을 제조하는 단계, 발포-형성 조성물을 기판에 적용시키는 단계 및 발포-형성 조성물을 발포시켜 경화시키는 단계를 포함하는, 기판에 대한 실리콘 발포체의 접착을 증진시키는 방법을 제공한다.The invention also relates to polyorganosiloxanes containing an average of at least two alkenyl radicals per molecule, organohydrogensiloxanes having an average of at least two silicon-bonded hydrogens per molecule, blowing agents, platinum catalysts, and epoxy-functional compounds ; Compounds comprising at least one alkenyl group in the same molecule as at least one hydroxy group; Tetraalkylorthosilicates; Preparing a foam-forming composition comprising an organotitanate and an adhesion promoter comprising an aluminum compound or a zirconium compound, applying the foam-forming composition to a substrate, and foaming and curing the foam-forming composition To provide a method of promoting the adhesion of the silicone foam to the substrate.
본 발명의 오가노실록산 조성물은The organosiloxane composition of the present invention
(A) 분자당 평균 2개 이상의 알케닐 라디칼을 함유하는 폴리오가노실록산;(A) polyorganosiloxanes containing on average two or more alkenyl radicals per molecule;
(B) 분자당 평균 2개 이상의 규소-결합된 수소 원자를 갖는 오가노하이드로겐실록산;(B) organohydrogensiloxanes having an average of at least two silicon-bonded hydrogen atoms per molecule;
(C) 발포제;(C) blowing agents;
(D) 백금 촉매 및(D) platinum catalysts and
(E) i) 에폭시-작용성 화합물;(E) i) epoxy-functional compounds;
ii) 하나 이상의 하이드록시 그룹과 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 하이드록실 작용성 화합물;ii) a hydroxyl functional compound comprising at least one alkenyl group in the same molecule as at least one hydroxy group;
iii) 테트라알킬오르토실리케이트;iii) tetraalkylorthosilicates;
iv) 오가노티타네이트 및iv) organotitanate and
v) 알루미늄 화합물 또는 지르코늄 화합물을 포함하는 접착 촉진제를 포함하며, 여기서, 성분 (A)중 알케닐 그룹의 평균 수와 성분(B)중의 규소-결합된 수소 그룹의 평균 수의 합은 4이상이다.v) an adhesion promoter comprising an aluminum compound or a zirconium compound, wherein the sum of the average number of alkenyl groups in component (A) and the average number of silicon-bonded hydrogen groups in component (B) is at least 4 .
성분 (A)는 분자당 평균 2개 이상의 알케닐 그룹을 함유하는 폴리오가노실록산이다. 이것은 본 발명의 조성물의 주요 성분이다. 본 발명의 조성물을 적절하게 가교결합시키기 위해서는, 성분 (A)가 분자당 평균 2개 이상의 알케닐 그룹을 함유하여야 한다. 바람직한 양태에서, 성분 (A)는 탄소수 2 내지 12의 알케닐 그룹을 함유한다. 바람직한 알케닐 그룹은 화학식 -R1CH=CH2(여기서, R1은 단일 결합 또는 탄소수 2 내지 10의 알킬렌 그룹이다)로 나타내어진다. 알킬렌 그룹은 직쇄 또는 측쇄일 수 있다. 바람직한 알케닐 그룹의 예는 비닐, 2-프로페닐, 3-부테닐, 5-헥세닐, 7-옥테닐 및 10-운데세닐을 포함한다. 더욱 바람직한 알케닐 그룹은 비닐 및 헥세닐이다. 바람직한 양태에서, 하나 이상의 알케닐 그룹은 분자 쇄의 말단에 위치한다. 더욱 바람직한 양태에서, 2개 이상의 알케닐 그룹은 분자 쇄의 2개의 말단에 위치한다.Component (A) is a polyorganosiloxane containing on average two or more alkenyl groups per molecule. This is the main component of the composition of the present invention. In order to properly crosslink the composition of the invention, component (A) must contain an average of at least two alkenyl groups per molecule. In a preferred embodiment, component (A) contains alkenyl groups of 2 to 12 carbon atoms. Preferred alkenyl groups are represented by the formula -R 1 CH = CH 2 , wherein R 1 is a single bond or an alkylene group having 2 to 10 carbon atoms. The alkylene group may be straight or branched chain. Examples of preferred alkenyl groups include vinyl, 2-propenyl, 3-butenyl, 5-hexenyl, 7-octenyl and 10-undecenyl. More preferred alkenyl groups are vinyl and hexenyl. In a preferred embodiment, at least one alkenyl group is located at the end of the molecular chain. In a more preferred embodiment, two or more alkenyl groups are located at two ends of the molecular chain.
바람직한 양태에서, 성분 (A)는 화학식In a preferred embodiment, component (A) is of formula
(여기서, 각각의 R2는 별개로 탄소수 1 내지 20의 비치환된 일가 탄화수소 그룹 및 치환된 일가 탄화수소 그룹중에서 선택되고; R3은 R2또는 알케닐 그룹이며; m은 0이상이고; n은 성분 (A)가 분자당 평균 2개 이상의 알케닐 그룹을 갖도록 선택된다)로 나타내어진다.Wherein each R 2 is independently selected from an unsubstituted monovalent hydrocarbon group and a substituted monovalent hydrocarbon group having 1 to 20 carbon atoms; R 3 is R 2 or an alkenyl group; m is at least 0; n is Component (A) is selected to have an average of at least two alkenyl groups per molecule).
바람직하게는, R2는 탄소수 7미만의 비치환된 일가 탄화수소 그룹 또는 탄소수 7미만의 할로겐화된 알킬 그룹이다. 더욱 바람직하게는, R2는 메틸 또는 에틸과 같은 알킬 그룹, 사이클로헥실과 같은 사이클로알킬 그룹, 페닐과 같은 아릴 그룹 또는 클로로메틸, 3-클로로프로필 또는 3,3,3-트리플루오로프로필과 같은 할로겐화된 알킬 그룹이다. 가장 바람직하게는, R2는 메틸이다. 바람직한 양태에서, n은 0이다.Preferably, R 2 is an unsubstituted monovalent hydrocarbon group of less than 7 carbon atoms or a halogenated alkyl group of less than 7 carbon atoms. More preferably, R 2 is an alkyl group such as methyl or ethyl, a cycloalkyl group such as cyclohexyl, an aryl group such as phenyl or such as chloromethyl, 3-chloropropyl or 3,3,3-trifluoropropyl Halogenated alkyl group. Most preferably, R 2 is methyl. In a preferred embodiment, n is zero.
일반적으로 실록산은 25℃에서 0.03 내지 500Pa·s, 바람직하게는 2 내지 250 Pa·s의 점도로 중합된다. 더욱 높거나 낮은 점도의 중합체도 사용가능하다.Generally the siloxanes are polymerized at 25 ° C. with a viscosity of 0.03 to 500 Pa · s, preferably 2 to 250 Pa · s. Higher or lower viscosity polymers may also be used.
본 발명의 폴리오가노실록산은 단독중합체 또는 공중합체일 수 있다. 단일 폴리오가노실록산이 사용되거나 상이한 폴리오가노실록산의 혼합물이 사용될 수 있다.The polyorganosiloxane of the present invention may be a homopolymer or a copolymer. Single polyorganosiloxanes may be used or mixtures of different polyorganosiloxanes may be used.
성분 (A)의 폴리오가노실록산을 제조하는 방법은 본 명세서에서 상세한 설명이 필요하지 않을 정도로 특허 및 기타 문헌에 기재되어 있다.The process for preparing the polyorganosiloxane of component (A) is described in patents and other documents to the extent that no detailed description is required herein.
성분 (B)는 분자당 평균 2개 이상의 실리콘-결합된 수소 원자를 함유하는 오가노하이드로겐실록산이다. 이것은 본 발명의 조성물을 가교결합시키는데 사용된다. 성분 (B)중 실리콘-결합된 수소 원자는 조성물을 경화시키기 위하여 성분 (A)중의 알케닐 그룹과 반응한다. 조성물을 실리콘 탄성체로 경화시키기 위해서는, 성분 (A)중 분자당 규소-결합된 알케닐 그룹의 평균 수와 성분 (B)중 분자당 규소-결합된 수소 원자의 평균 수의 합이 4이상이어야 한다. 사용된 성분 (B)의 수소 함량 및 양에 따라, 오가노실록산중 실리콘 결합된 수소 원자가 본 발명의 조성물을 발포시키기 위한 가스를 생성시키는데 사용될 수 있다.Component (B) is an organohydrogensiloxane containing on average two or more silicon-bonded hydrogen atoms per molecule. It is used to crosslink the composition of the present invention. The silicon-bonded hydrogen atoms in component (B) react with the alkenyl groups in component (A) to cure the composition. In order to cure the composition with silicone elastomer, the sum of the average number of silicon-bonded alkenyl groups per molecule in component (A) and the average number of silicon-bonded hydrogen atoms per molecule in component (B) must be at least four. . Depending on the hydrogen content and amount of component (B) used, silicon-bonded hydrogen atoms in the organosiloxane can be used to produce a gas for foaming the compositions of the present invention.
성분 (B)로서 사용될 수 있는 오가노하이드로겐실록산은 바람직하게는 분자당 평균 2개 이상의 규소-결합된 수소 원자를 함유하며, 더욱 바람직하게는 분자당 평균 3개 이상의 규소-결합된 수소 원자를 함유한다. 실리콘 원자상의 나머지 원자가는 탄소수 7미만의 알킬 그룹, 탄소수 7미만의 할로겐화된 알킬 그룹 및 아릴 그룹중에서 선택된 유기 그룹에 의해 충족된다. 바람직한 아릴 그룹은 페닐이다. 바람직한 알킬 그룹은 메틸, 에틸 및 헥실이다. 가장 바람직한 알킬 그룹은 메틸 그룹이다. 바람직한 할로겐화 알킬 그룹은 3,3,3-트리플루오로프로필이다.Organohydrogensiloxanes which can be used as component (B) preferably contain an average of at least two silicon-bonded hydrogen atoms per molecule, more preferably an average of at least three silicon-bonded hydrogen atoms per molecule. It contains. The remaining valence on the silicon atom is met by an organic group selected from alkyl groups of less than 7 carbon atoms, halogenated alkyl groups of less than 7 carbon atoms and aryl groups. Preferred aryl group is phenyl. Preferred alkyl groups are methyl, ethyl and hexyl. Most preferred alkyl groups are methyl groups. Preferred halogenated alkyl groups are 3,3,3-trifluoropropyl.
성분 (B)의 오가노하이드로겐실록산은 직쇄 또는 측쇄 구조를 가질 수 있으며 단독중합체, 공중합체 또는 이러한 유형의 중합체의 혼합물일 수 있다.The organohydrogensiloxane of component (B) may have a straight or branched chain structure and may be a homopolymer, a copolymer or a mixture of polymers of this type.
성분 (B)로서 사용하기에 적합한 중합체는 폴리메틸하이드로겐실록산, 트리메틸실록시-말단 폴리메틸하이드로겐실록산, 디메틸실록산, 메틸하이드로겐실록산 및 트리메틸실록산 단위의 공중합체 및 디메틸실록산, 메틸하이드로겐실록산 및 디메틸하이드록겐실록산 단위의 공중합체로 예시된다.Suitable polymers for use as component (B) include copolymers of polymethylhydrogensiloxane, trimethylsiloxy-terminated polymethylhydrogensiloxane, dimethylsiloxane, methylhydrogensiloxane and trimethylsiloxane units and dimethylsiloxane, methylhydrogensiloxane And copolymers of dimethylhydroxylsiloxane units.
바람직한 직쇄형 오가노하이드로겐실록산의 점도는 25℃에서 0.01 내지 10Pa·s이고 디알킬실록산 및 트리알킬실록시 말단 단위를 갖는 알킬하이드로겐실록산 단위를 포함한다. 알킬 그룹의 탄소수는 1 내지 4이며 가장 바람직하게는 메틸이다. 바람직한 양태에서, 성분 (B)는 2개 유형의 오가노하이드로겐실록산을 포함하며, 이중 하나는 폴리메틸하이드로겐실록산이고, 다른 것은 메틸하이드로겐실록산과 디메틸실록산 단위를 함유하는 공중합체이다.Preferred straight chain organohydrogensiloxanes have a viscosity of from 0.01 to 10 Pa · s at 25 ° C. and include alkylhydrogensiloxane units having dialkylsiloxane and trialkylsiloxy terminal units. The alkyl group has 1 to 4 carbon atoms and most preferably methyl. In a preferred embodiment, component (B) comprises two types of organohydrogensiloxanes, one of which is a polymethylhydrogensiloxane and the other is a copolymer containing methylhydrogensiloxane and dimethylsiloxane units.
사용된 성분 (B)의 부위는 경화동안 바람직한 가교결합도를 제공하고 혼합물을 발포시키는데 필요한 양의 수소 가스를 생성하기에 충분하여야 한다. 일반적으로, 본 발명의 조성물중 성분 (B)의 비는 성분 (A) 100부당 1 내지 40중량부의 범위의 양이다. 바람직한 양태에서, 성분 (B)는 성분 (A) 100부당 5 내지 30부 범위의 양으로 존재한다. 더욱 바람직한 양태에서, 성분 (B)는 성분 (A) 100부당 7 내지 20부 범위의 양으로 존재한다.The site of component (B) used should be sufficient to provide the desired degree of crosslinking during curing and to produce the amount of hydrogen gas necessary to foam the mixture. In general, the ratio of component (B) in the composition of the present invention is in an amount ranging from 1 to 40 parts by weight per 100 parts of component (A). In a preferred embodiment, component (B) is present in an amount ranging from 5 to 30 parts per 100 parts of component (A). In a more preferred embodiment, component (B) is present in an amount ranging from 7 to 20 parts per 100 parts of component (A).
하이드로실레이션 반응에 의해 경화가능한 조성물중 비닐 또는 기타 에틸렌적으로 불포화된 탄화수소 그룹에 대한 규소-결합된 수소 원자의 몰비는 경화된 탄성체의 특성에 있어 중요하다. 본 발명의 경화가능한 조성물의 최적 비는 분자중량부 이상의 폴리오가노실록산 및 가교결합제의 유형에 의해 결정될 것이다. 본 발명의 조성물중 오가노하이드로겐실록산(성분 (B)) 및 폴리오가노실록산(성분 (A))의 상대 농도는 규소-결합된 수소 원자 대 알케닐 라디칼의 몰비에 상당하며 통상적으로 3.5:1 내지 7.5:1을 형성한다.The molar ratio of silicon-bonded hydrogen atoms to vinyl or other ethylenically unsaturated hydrocarbon groups in the composition curable by the hydrosilylation reaction is important for the properties of the cured elastomer. The optimal ratio of the curable composition of the present invention will be determined by the type of polyorganosiloxane and crosslinking agent of at least molecular weight. The relative concentrations of organohydrogensiloxane (component (B)) and polyorganosiloxane (component (A)) in the compositions of the present invention correspond to the molar ratio of silicon-bonded hydrogen atoms to alkenyl radicals and are typically 3.5: 1. To 7.5: 1.
성분 C는 발포제이다. 조성물은 하나 이상의 발포제를 함유할 수 있다. 본 발명의 조성물용 발포제로 사용될 수 있는 화합물은 사용시 가스를 생성하는 화합물 또는 휘발되어 가스성 상태가 되는 화합물이다. 이러한 화합물은 물, 알콜, 실라놀 및 기타 -OH 함유 화합물로 예시된다. 알콜은 유기 알콜 및 일작용성 알콜 및 폴리올을 포함하도록 사용될 수 있는 유기 알콜이다. 바람직한 일작용성 알콜은 분자당 탄소수가 1 내지 12이고 하나 이상의 하이드록실 그룹을 갖는 유기 알콜이다. 유기 알콜의 골격을 형성하는 탄소 쇄는 직쇄 또는 측쇄일 수 있으며 또한 하이드록실 그룹이 직접 결합되어 있지 않은 방향족 환을 지닐 수 있다. 발포제로서 사용가능한 일작용성 알콜의 예는 메탄올, 에탄올, n-프로판올, 이소프로판올, n-부탄올, 2-부탄올, 3급-부탄올, n-옥타놀 및 벤질 알콜을 포함한다. 바람직한 일작용성 알콜은 벤질 알콜이다. 바람직한 폴리올은 탄소수가 3 내지 12이며 분자당 평균 2개 이상의 하이드록실 그룹을 함유하는 유기 알콜이다. 폴리올의 골격을 구성하는 탄소 쇄는 직쇄 또는 측쇄일 수 있으며 하이드록실 그룹이 직접 결합되지 않는 방향족 환을 지닐 수 있다. 바람직한 폴리올은 디올이다. 바람직한 디올은 1,4-부탄디올, 1,5-펜탄디올 및 1,7-헵탄이올이다. 본 발명의 조성물용으로 바람직한 발포제는 일작용성 알콜이다. 더욱 바람직한 발포제는 일작용성 알콜이다.Component C is a blowing agent. The composition may contain one or more blowing agents. Compounds which can be used as blowing agents for the compositions of the present invention are compounds which produce gas when in use or compounds which volatilize to a gaseous state. Such compounds are exemplified by water, alcohols, silanol and other -OH containing compounds. Alcohols are organic alcohols that can be used to include organic alcohols and monofunctional alcohols and polyols. Preferred monofunctional alcohols are organic alcohols having 1 to 12 carbon atoms per molecule and having at least one hydroxyl group. The carbon chains that form the backbone of the organic alcohol can be straight or branched chains and can also have aromatic rings to which hydroxyl groups are not directly bonded. Examples of monofunctional alcohols usable as blowing agents include methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, tert-butanol, n-octanol and benzyl alcohol. Preferred monofunctional alcohols are benzyl alcohols. Preferred polyols are organic alcohols having 3 to 12 carbon atoms and containing on average two or more hydroxyl groups per molecule. The carbon chain constituting the backbone of the polyol may be straight or branched and may have an aromatic ring to which hydroxyl groups are not directly bonded. Preferred polyols are diols. Preferred diols are 1,4-butanediol, 1,5-pentanediol and 1,7-heptaneol. Preferred blowing agents for the compositions of the present invention are monofunctional alcohols. More preferred blowing agents are monofunctional alcohols.
충분한 발포제는 발포 과정동안 필요한 양의 수소 가스를 수득하는데 사용되어야 한다. 일반적으로, 성분 (C) 0.1 내지 20중량부가 성분 (A) 및 (B)의 합한 중량 100중량부당 사용되어야 한다. 성분 (C)의 바람직한 양은 성분 (A) 및 (B)의 합한 중량 100중량부당 0.1 내지 15중량부이다. 성분 (C)의 더욱 바람직한 양은 성분 (A) 및 (B) 100중량부당 5 내지 13중량부이다.Sufficient blowing agent should be used to obtain the required amount of hydrogen gas during the foaming process. In general, 0.1 to 20 parts by weight of component (C) should be used per 100 parts by weight of the combined weight of components (A) and (B). The preferred amount of component (C) is 0.1 to 15 parts by weight per 100 parts by weight of the combined weight of components (A) and (B). More preferred amounts of component (C) are 5 to 13 parts by weight per 100 parts by weight of components (A) and (B).
성분 (D)는 주기율 표의 백금족으로부터의 금속 또는 이러한 금속의 화합물이다. 이러한 금속은 백금, 팔라듐 및 로듐을 포함한다. 백금 및 백금 화합물들이 하이드로실레이션 반응에 있어 이들 촉매의 고 활성도를 기준으로 할 때 바람직하다. 본 발명의 오가노실록산 조성물중 성분 (D)로서 사용될 수 있는 촉매는 -SiH 그룹과 규소-결합된 알케닐 그룹의 반응을 촉진시키는데 효과적인 모든 공지된 형태이다. 이러한 촉매는 또한 SiH 및 유기 알콜내 ≡COH 그룹간의 반응을 촉진하여 발포 과정을 위한 수소를 제공하기에 효율적이다.Component (D) is a metal from the platinum group of the periodic table or a compound of such a metal. Such metals include platinum, palladium and rhodium. Platinum and platinum compounds are preferred based on the high activity of these catalysts in hydrosilylation reactions. Catalysts that can be used as component (D) in the organosiloxane composition of the present invention are all known forms that are effective for catalyzing the reaction of -SiH groups with silicon-bonded alkenyl groups. These catalysts are also efficient to promote the reaction between SiH and the —COH groups in organic alcohols to provide hydrogen for the foaming process.
백금의 적합한 형태는 클로로플라틴산, 백금 화합물 및 백금 화합물과 불포화된 유기 화합물 또는 에틸렌적으로 불포화된 그룹을 함유하는 규소-결합된 그룹을 갖는 실록산의 착체로 예시될 수 있다. 적합한 백금 촉매의 추가 예는 플라티너스 할라이드 또는 클로로플라틴산과 디비닐테트라메틸디실록산 및 테트라메틸디실록산의 착체를 포함한다. 적합한 백금 촉매는 미국 특허 제3,419,593호에 기술되어 있다.Suitable forms of platinum can be exemplified by the complexes of chloroplatinic acid, platinum compounds and siloxanes with platinum compounds and silicon-bonded groups containing unsaturated organic compounds or ethylenically unsaturated groups. Further examples of suitable platinum catalysts include complexes of platinum halides or chloroplatinic acid with divinyltetramethyldisiloxane and tetramethyldisiloxane. Suitable platinum catalysts are described in US Pat. No. 3,419,593.
본 발명의 조성물중 성분 (D)의 농도는 성분 (A) 및 (B)의 합한 중량을 기준으로하여, 백만부(ppm)당 백금 금속 0.1 내지 500중량부, 바람직하게는 백금 금속 5 내지 250중량부 및 더욱 바람직하게는 백금 금속 25 내지 100중량부의 백금 농도에 상당한다.The concentration of component (D) in the composition of the present invention is 0.1 to 500 parts by weight, preferably 5 to 250 parts by weight, of platinum metal per million parts (ppm), based on the combined weight of components (A) and (B). Parts, and more preferably 25 to 100 parts by weight of platinum metal.
성분 (E)는 접착 촉진제이다. 본 발명의 접착 촉진제는 (i) 에폭시-작용성 화합물; (ii) 하나 이상의 하이드록실 그룹과 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 하이드록실-작용성 화합물; (iii) 테트라알킬오르토실리케이트; (iv) 오가노티타네이트 및 (v) 알루미늄 화합물 또는 지르코늄 화합물을 포함한다.Component (E) is an adhesion promoter. Adhesion promoters of the invention include (i) epoxy-functional compounds; (ii) a hydroxyl-functional compound comprising at least one alkenyl group in the same molecule as the at least one hydroxyl group; (iii) tetraalkylorthosilicates; (iv) organotitanate and (v) aluminum compound or zirconium compound.
성분 (i)는 에폭시-작용성 화합물이다. 본 발명의 조성물중에 사용될 수 있는 에폭시-작용성 화합물의 예는 일본 공개공보 제60-101146호; EP 제0,497,349호 및 미국 특허 제4,087,585호에 기술되어 있다. 에폭시 작용성 화합물은 다음 화학식 1 내지 화학식 4의 비-규소 함유 화합물일 수 있다.Component (i) is an epoxy-functional compound. Examples of epoxy-functional compounds which can be used in the compositions of the present invention are disclosed in Japanese Patent Application Laid-Open No. 60-101146; EP 0,497,349 and US Pat. No. 4,087,585. The epoxy functional compound may be a non-silicon containing compound of the following formulas (1) to (4).
상기식에서,In the above formula,
Bu는 부틸이고,Bu is butyl,
Me는 메틸이다.Me is methyl.
에폭시-작용성 화합물은 화학식 5 내지 화학식 7로 나타내어지는 랜덤 또는 블록 실록산 공중합체일 수 있다.The epoxy-functional compound may be a random or block siloxane copolymer represented by Formulas 5-7.
상기식에서,In the above formula,
Q는 화학식이고,Q is a chemical formula ego,
a, b 및 c는 양의 정수이며,a, b and c are positive integers,
d는 0 또는 양의 정수이고,d is 0 or a positive integer,
z는 양의 정수이며,z is a positive integer,
x 및 y는 0 또는 양의 정수이고,x and y are zero or a positive integer,
총 3 ≥ (x+y+z) ≤ 8이며,3 ≥ (x + y + z) ≤ 8 in total,
e의 값은 3 내지 10의 범위이고, 바람직한 e의 값은 3이다.The value of e is in the range of 3 to 10, and the preferred value of e is 3.
바람직한 에폭시-작용성 화합물은 화학식 8의 에폭시-작용성 알콕시실란이다.Preferred epoxy-functional compounds are epoxy-functional alkoxysilanes of formula (8).
상기식에서,In the above formula,
R4는 탄소수 1 내지 10의 포화되고 치환되거나 비치환된 탄화수소이고,R 4 is a saturated, substituted or unsubstituted hydrocarbon having 1 to 10 carbon atoms,
R5는 탄소수 1 내지 10의 비치환된 알킬이며,R 5 is unsubstituted alkyl having 1 to 10 carbon atoms,
m 및 n은 1, 2 또는 3이고,m and n are 1, 2 or 3,
m + n은 2, 3 또는 4이며,m + n is 2, 3 or 4,
e는 3 내지 10이다.e is 3 to 10.
에폭시 작용성 알콕시실란에 있어서, R4는 메틸, 에틸, 페닐 및 3,3,3-트리플루오로프로필일 수 있다. R4가 메틸인 경우 바람직하다. 에폭시-작용성 알콕시실란에 있어서, R5는 메틸, 에틸, 프로필 및 3급-부틸일 수 있다. R5가 메틸인 경우 바람직하다. 에폭시-작용성 알콕시실란에 있어서 m이 2이상인 경우가 바람직하고 m이 3인 경우가 가장 바람직하다. 본 발명의 조성물에 사용하기 위한 바람직한 에폭시-작용성 알콕시실란은 글리시독시프로필트리메톡시실란이다.For epoxy functional alkoxysilanes, R 4 can be methyl, ethyl, phenyl and 3,3,3-trifluoropropyl. It is preferred if R 4 is methyl. For epoxy-functional alkoxysilanes, R 5 can be methyl, ethyl, propyl and tert-butyl. It is preferred when R 5 is methyl. In the epoxy-functional alkoxysilane, the case where m is 2 or more is preferable, and the case where m is 3 is most preferable. Preferred epoxy-functional alkoxysilanes for use in the compositions of the present invention are glycidoxypropyltrimethoxysilane.
에폭시-작용성 화합물은 본 발명의 경화가능한 오가노실록산 조성물에 성분 (A) 100부당 0.01 내지 10중량부 및 바람직하게는 0.4 내지 5중량부의 농도에서 가해진다.The epoxy-functional compound is added to the curable organosiloxane composition of the present invention at a concentration of 0.01 to 10 parts by weight and preferably 0.4 to 5 parts by weight per 100 parts of component (A).
성분 (ii)는 하나 이상의 하이드록시 그룹 및 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 화합물이다. 성분 (ii)는 바람직하게는 알콕시 그룹을 포함하지 않는다. 성분 (ii)는 화학식 9의 카비놀 작용성 유기 화합물; 화학식 10의 실란; 화학식 11의 카비놀 작용성 실란; 화학식 12의 하이드록시 말단-종결된 실록산 및 화학식 13의 실록산일 수 있다.Component (ii) is a compound comprising at least one hydroxy group and at least one alkenyl group in the same molecule. Component (ii) preferably does not comprise alkoxy groups. Component (ii) is a carbinol functional organic compound of formula 9; Silanes of Formula 10; Carbinol functional silanes of Formula 11; Hydroxy end-terminated siloxanes of Formula 12 and siloxanes of Formula 13.
상기식에서,In the above formula,
R6은 탄소수 1 내지 15의 이가 탄화수소 라디칼이고,R 6 is a divalent hydrocarbon radical of 1 to 15 carbon atoms,
각각의 R7은 독립적으로 탄소수 1 내지 20의 포화된 탄화수소 라디칼중에서 선택되며,Each R 7 is independently selected from saturated hydrocarbon radicals having 1 to 20 carbon atoms,
R8은 알케닐 그룹이고,R 8 is an alkenyl group,
f는 0 내지 2이며,f is 0 to 2,
g는 1 내지 3이고,g is 1 to 3,
f + g는 2 또는 3이며,f + g is 2 or 3,
h는 0 내지 2이고,h is 0 to 2,
i는 1 내지 3이며,i is 1 to 3,
h + i는 1 내지 3이고,h + i is 1 to 3,
각각의 R9는 독립적으로 탄소수 12미만의 포화된 비치환되거나 치환된 탄화수소중에서 선택되며,Each R 9 is independently selected from saturated unsubstituted or substituted hydrocarbons having less than 12 carbon atoms,
p는 1 내지 40이고,p is 1 to 40,
t는 0 내지 18이며,t is from 0 to 18,
p + t는 2 내지 40이고,p + t is from 2 to 40,
R10은 카비놀 작용성의 지방족 또는 방향족 라디칼이며,R 10 is a carbinol functional aliphatic or aromatic radical,
j 및 k는 1이상이고,j and k are 1 or more,
L은 0이상이며,L is 0 or more,
j + k + L은 2 내지 150이다.j + k + L is 2 to 150.
화학식 9의 카비놀 작용성 화합물에 있어서, R6은 메틸렌, 에틸렌 및 프로필렌과 같은 알킬렌 또는 페닐렌과 같은 아릴렌일 수 있다.In the carbinol functional compound of formula 9, R 6 may be alkylene such as methylene, ethylene and propylene or arylene such as phenylene.
화학식 10의 실란에 있어서, R7은 메틸, 에틸, 3급-부틸, 사이클로펜탄, 사이클로헥산 및 페닐이고, R8은 비닐, 아릴 또는 헥세닐과 같은 알케닐이다. 화학식 10의 유용한 실란 화합물의 예는 미국 특허 제4,659,851호에서 찾을 수 있다.In the silane of formula 10, R 7 is methyl, ethyl, tert-butyl, cyclopentane, cyclohexane and phenyl and R 8 is alkenyl such as vinyl, aryl or hexenyl. Examples of useful silane compounds of formula 10 can be found in US Pat. No. 4,659,851.
화학식 12 및 13에 있어서, R9는 메틸, 에틸 및 프로필과 같은 알킬, 3,3,3-트리플루오로프로필과 같은 치환된 알킬, 페닐과 같은 아릴 및 사이클로펜틸 및 사이클로헥실과 같은 사이클로알킬일 수 잇다. R9가 메틸인 경우가 바람직하다. 화학식 12 및 13에 있어서, 각각의 R8은 전술한 바와 같다. R8이 비닐인 경우가 바람직하다.In formulas 12 and 13, R 9 is alkyl such as methyl, ethyl and propyl, substituted alkyl such as 3,3,3-trifluoropropyl, aryl such as phenyl and cycloalkylyl such as cyclopentyl and cyclohexyl Can be. It is preferred if R 9 is methyl. In Formulas 12 and 13, each R 8 is as described above. It is preferred if R 8 is vinyl.
바람직한 성분(ii)는 화학식 12의 하이드록시 말단-종결된 실록산이다. R8이 비닐이고, R9가 메틸이며, p가 1이고, t가 4인 화학식 12의 하이드록시 말단-종결된 실록산이 더욱 바람직하다.Preferred component (ii) is a hydroxy end-terminated siloxane of formula 12. More preferred are hydroxy end-terminated siloxanes of formula (12) wherein R 8 is vinyl, R 9 is methyl, p is 1 and t is 4.
본 발명의 조성물에 가해진 성분 (ii)의 양은 성분 (A) 100부당 0.01 내지 5부이다. 성분 (A) 100부당 성분 (ii) 0.1 내지 2부를 가하는 경우가 바람직하다.The amount of component (ii) added to the composition of the present invention is 0.01 to 5 parts per 100 parts of component (A). It is preferable to add 0.1-2 parts of component (ii) per 100 parts of component (A).
성분 (iii)는 테트라알킬오르토실리케이트이다. 테트라알킬오르토실리케이트의 탄소수는 바람직하게는 1 내지 6이며 더욱 바람직하게는 2 내지 3이다. 테트라에틸오르토실리케이트가 가장 바람직하다. 성분 (iii)은 성분 (A) 100부당 0.1 내지 5중량부 범위의 양으로 존재한다. 바람직한 양태에서, 본 발명의 조성물은 성분 (A) 100부당 성분 (iii) 0.6 내지 3.0부를 함유한다.Component (iii) is tetraalkylorthosilicate. The carbon number of the tetraalkylorthosilicate is preferably 1 to 6, more preferably 2 to 3. Tetraethylorthosilicate is most preferred. Component (iii) is present in amounts ranging from 0.1 to 5 parts by weight per 100 parts of component (A). In a preferred embodiment, the composition of the present invention contains 0.6 to 3.0 parts of component (iii) per 100 parts of component (A).
성분 (iv)는 오가노티타네이트이다. 바람직한 오가노티타네이트는 테트라알킬티타네이트이다. 바람직한 테트라알킬티타네이트는 테트라부틸티타네이트이다. 성분 (iv)는 성분 (A) 100부당 0.01 내지 1중량부 범위의 양으로 존재한다. 바람직한 양태에서, 본 발명의 조성물은 성분 (iv) 0.1 내지 1.0중량부를 함유한다. 성분 (iv) 0.01부 미만을 함유하는 조성물로부터 제조된 실리콘 발포체가 저온에서 경화되는 경우, 이들은 플라스틱 및 기타 기판에 대한 접착을 나타내지 않는다.Component (iv) is an organotitanate. Preferred organo titanates are tetraalkyl titanates. Preferred tetraalkyl titanates are tetrabutyl titanates. Component (iv) is present in an amount ranging from 0.01 to 1 part by weight per 100 parts of component (A). In a preferred embodiment, the composition of the present invention contains 0.1 to 1.0 parts by weight of component (iv). When silicone foams made from compositions containing less than 0.01 part of component (iv) are cured at low temperatures, they do not exhibit adhesion to plastics and other substrates.
성분 (v)를 구성하는 알루미늄 화합물 또는 지르코늄 화합물은 성분 (i) 내지 (iv)와 함께 사용됨으로써 본 발명의 경화가능한 오가노폴리실록산 조성물의 접착을 증진시키는데 제공된다. 유용한 알루미늄 화합물 및 지르코늄 화합물은 미국 특허 제4,742,103호 및 일본 특허공개공보 제60-101146호에 교시되어 있다. 알루미늄 화합물 또는 지르코늄 화합물은 알콕사이드, 펜옥사이드 및 카복실레이트를 포함하는 알콜레이트 및 하나 이상의 알콕사이드, 펜옥사이드 또는 카복실 그룹이 유기 리간드 또는 성분 (i)에서 유래된 유기규소 그룹으로 대체된 화합물일 수 있다. 알콕시 그룹은 메톡시, 에톡시 및 이소-프로폭시로 예시되며, 펜록시 그룹은 펜록시 및 p-메틸펜록시로 예시되고, 카본옥실 그룹은 아세톡시, 프로피오닐록시, 이소프로피오닐록시, 부티르록시 및 스테아로일록시로 예시된다. 알루미늄 화합물 또는 지르코늄 화합물은 알루미늄 알콜레이트 또는 지르코늄 알콜레이트와 아세토아세테이트 또는 디알킬말로네이트의 반응에 의해 수득된 것과 같은 킬레이트일 수 있다. 알루미늄 화합물 또는 지르코늄 화합물은 산화알루미늄 또는 산화지르코늄의 유기 염일 수 있거나 알루미늄 아세틸아세토네이트 또는 지르코늄 아세틸아세토네이트일 수 있다.The aluminum compound or zirconium compound constituting component (v) is provided to promote adhesion of the curable organopolysiloxane composition of the present invention by being used with components (i) to (iv). Useful aluminum compounds and zirconium compounds are taught in US Pat. No. 4,742,103 and Japanese Patent Laid-Open No. 60-101146. The aluminum compound or zirconium compound may be an alcoholate comprising alkoxides, phenoxides and carboxylates and compounds in which one or more alkoxides, phenoxides or carboxyl groups are replaced with organosilicon groups derived from an organic ligand or component (i). Alkoxy groups are exemplified by methoxy, ethoxy and iso-propoxy, phenoxy groups are exemplified by phenoxy and p-methylphenoxy, and carbonoxyl groups are acetoxy, propionyloxy, isopropionyloxy, minor Exemplified by tyroxy and stearoyloxy. The aluminum compound or zirconium compound may be a chelate such as obtained by reaction of aluminum alcoholate or zirconium alcoholate with acetoacetate or dialkylmalonate. The aluminum compound or zirconium compound may be an organic salt of aluminum oxide or zirconium oxide or may be aluminum acetylacetonate or zirconium acetylacetonate.
알루미늄 화합물이 본 발명의 조성물에 있어 바람직하다. 유용한 알루미늄 화합물은 알루미늄 아세틸아세토네이트, 알루미늄 트리이소프로폭사이드, 알루미늄 트리-t-부톡사이드, 알루미늄 트리아세테이트, 알루미늄 트리스테아레이트, 알루미늄 트리벤조에이트, 비스에틸아세토아세테이트알루미늄 모노아세틸아세토네이트, 아세토알콕시알루미늄 디이소프로필레이트 및 알루미늄 2,4-펜탄디오네이트를 포함할 수 있다. 바람직한 알루미늄 화합물은 알루미늄 아세틸아세토네이트이다.Aluminum compounds are preferred for the compositions of the present invention. Useful aluminum compounds include aluminum acetylacetonate, aluminum triisopropoxide, aluminum tri-t-butoxide, aluminum triacetate, aluminum tristearate, aluminum tribenzoate, bisethylacetoacetate aluminum monoacetylacetonate, acetoalkoxy Aluminum diisopropylate and aluminum 2,4-pentanedionate. Preferred aluminum compounds are aluminum acetylacetonates.
성분 (v)로서 유용한 지르코늄 화합물은 기술된 알루미늄 화합물의 동족체이다. 특이적인 예는 Zr(OH)2(C2H3)2및 Zr{CH(COCH3)2}4이다.Zirconium compounds useful as component (v) are homologues of the aluminum compounds described. Specific examples are Zr (OH) 2 (C 2 H 3 ) 2 and Zr {CH (COCH 3 ) 2 } 4 .
성분 (v)는 본 발명의 조성물에 성분 (A) 100중량부당 0.0005 내지 1중량부, 바람직하게는 0.001 내지 0.2중량부의 범위내에서 가해진다. 성분 (v)가 너무 소량으로 존재하는 경우 접착이 증가되지 않는 반면, 과량의 첨가는 비경제적이고 압착 세트 및 가연성과 같은 경화 조성물의 물리적 특성에 악 영향을 미칠 수 있다.Component (v) is added to the composition of the present invention within the range of 0.0005 to 1 part by weight, preferably 0.001 to 0.2 part by weight per 100 parts by weight of component (A). Adhesion is not increased when component (v) is present in too small amounts, while the addition of excess is uneconomical and can adversely affect the physical properties of the cured composition, such as compression set and flammability.
본 발명은 또한The invention also
(I) (A) 분자당 평균 2개 이상의 알케닐 라디칼을 함유하는 폴리오가노실록산;(I) (A) polyorganosiloxanes containing on average two or more alkenyl radicals per molecule;
(B) 분자당 평균 2개 이상의 규소-결합된 수소 원자를 갖는 오가노하이드로겐실록산;(B) organohydrogensiloxanes having an average of at least two silicon-bonded hydrogen atoms per molecule;
(C) 발포제;(C) blowing agents;
(D) 백금 촉매 및(D) platinum catalysts and
(E) i) 에폭시-작용성 화합물;(E) i) epoxy-functional compounds;
ii) 하나 이상의 하이드록시 그룹과 동일한 분자내에 하나 이상의 알케닐 그룹을 포함하는 하이드록실 작용성 화합물;ii) a hydroxyl functional compound comprising at least one alkenyl group in the same molecule as at least one hydroxy group;
iii) 테트라알킬오르토실리케이트;iii) tetraalkylorthosilicates;
iv) 오가노티타네이트 및iv) organotitanate and
v) 알루미늄 화합물 및 지르코늄 화합물을 포함하는 접착 촉진제를 포함하는 발포-형성 조성물[여기서, 성분 (A)중 분자당 알케닐 그룹의 평균 수와 성분(B)중의 규소-결합된 수소 그룹의 평균 수의 합은 4이상이다]을 제조하는 단계;v) a foam-forming composition comprising an adhesion promoter comprising an aluminum compound and a zirconium compound, wherein the average number of alkenyl groups per molecule in component (A) and the average number of silicon-bonded hydrogen groups in component (B) The sum of 4 or more];
(II) 조성물을 기판에 적용시키는 단계;(II) applying the composition to the substrate;
(III) 조성물이 발포체를 형성하도록 하는 단계 및(III) allowing the composition to form a foam and
(IV) 조성물이 경화되도록 하는 단계를 포함하는 기판에 대한 실리콘 발포체의 접착을 증진시키는 방법을 제공한다.(IV) providing a method of promoting adhesion of a silicone foam to a substrate comprising allowing the composition to cure.
본 발명의 방법은 성분 (A) 내지 (E) 모두와 임의 성분을 혼합함에 의해 발포성의 경화가능한 오가노실록산 조성물을 제조함으로써 수행한다. 성분이 균질하게 혼합되는 한, 혼합 방법은 임계적이지 않다. 혼합은 예를 들면, 수작업 또는 정적, 동적 또는 충돌-형 혼합 장치를 사용하여 수행할 수 있다. 성분 (A) 내지 (E) 및 임의 성분을 균질하게 혼합한 후, 발포-형성 조성물을 기판에 적용시킬 수 있다. 적용법은 임계적이지는 않으며 붓기, 분무 또는 분산을 포함한다. 적용법은 수작업이거나 자동 분산 장치를 사용할 수 있다. 발포성 조성물은 발포되어 기판상에서 경화된다. 기판은 바람직하게는 플라스틱이다. 바람직한 플라스틱은 아크릴로니트릴-부타디엔-스티렌 공중합체이다.The process of the present invention is carried out by preparing foamable curable organosiloxane compositions by mixing all of the components (A) to (E) with any of the components. As long as the components are mixed homogeneously, the mixing method is not critical. Mixing can be performed, for example, by hand or using a static, dynamic or collision-type mixing device. After homogeneously mixing components (A)-(E) and optional components, the foam-forming composition can be applied to the substrate. Application methods are not critical and include swelling, spraying or dispersing. The application method can be manual or use an automatic disperser. The foamable composition is foamed and cured on the substrate. The substrate is preferably plastic. Preferred plastics are acrylonitrile-butadiene-styrene copolymers.
발포-형성 조성물은 정상의 주위 온도에서 혼합이 개시된 즉시 발포되기 시작할 것이다. 경우에 따라, 발포 및 경화는 발포-형성 조성물중에 억제제를 포함시킴에 의해 지연시킬 수 있다. 비록 발포체의 경화가 정상의 주의 온도에서 일어날지라도, 기판에 대한 발포체의 접착은 발포체가 승온에서 경화되는 경우 증진될 것이다. 바람직한 양태에서, 발포체-형성 조성물은 75℃이상의 온도에서 최소 5분동안에 경화된다. 경화된 발포체는 또한 후-경화되어 경화된 발포체의 물리적 특성을 증진시킨다.The foam-forming composition will begin to foam at the start of mixing at normal ambient temperature. In some cases, foaming and curing may be delayed by including an inhibitor in the foam-forming composition. Although curing of the foam occurs at normal ambient temperatures, adhesion of the foam to the substrate will be enhanced if the foam cures at elevated temperatures. In a preferred embodiment, the foam-forming composition cures for at least 5 minutes at a temperature of at least 75 ° C. Cured foams are also post-cured to enhance the physical properties of the cured foams.
(A), (B), (C), (D) 및 (E)로 정의된 성분외에, 본 발명의 조성물은 경화가능한 조성물 및/또는 경화된 발포체의 특성을 개질시키기 위한 각종 성분을 함유할 수 있다.In addition to the components defined by (A), (B), (C), (D) and (E), the compositions of the present invention may contain various components for modifying the properties of the curable composition and / or cured foam. Can be.
이들 임의 성분은 석영 및 탄산 칼슘, 산화금속(예: 산화알루미나, 수화된 산화알루미나, 산화제2철 및 이산화티타늄)과 같은 미분된 강화성 광물 충진제 또는 비-강화성 광물 충진제; 탄소 블랙 및 산화아연과 같은 안료; 유기 안료 및 염료; 산화방지제; 열 안정화제; 자외선 안정화제; 난연제 및 경화가능한 조성물의 작업시간을 증가시키기 위한 사이클릭 메틸비닐실록산과 같은 촉매 억제제로 예시된다.These optional components include finely divided reinforcing mineral fillers or non-reinforcing mineral fillers such as quartz and calcium carbonate, metal oxides such as alumina oxide, hydrated alumina oxide, ferric oxide and titanium dioxide; Pigments such as carbon black and zinc oxide; Organic pigments and dyes; Antioxidants; Heat stabilizers; Ultraviolet stabilizers; Catalyst inhibitors such as cyclic methylvinylsiloxane for increasing the working time of flame retardants and curable compositions.
본 발명의 조성물중 바람직한 임의 성분은 트리오가노실록시 및 SiO4/2단위를 함유하는 수지성 유기실록산 공중합체이다. 이러한 유형의 공중합체중 트리오가노실록시 단위는 화학식 R11 3SiO1/2(여기서, R11은 일가의 비치환되거나 치환된 탄화수소 라디칼이다)로 나타낼 수 있다. 바람직한 공중합체에 있어서, R11로 나타낸 탄화수소 라디칼은 저급 알킬, 가장 바람직하게는 메틸의 배합이다. 공중합체내 트리오가노실록시 단위 대 SiO4/2단위의 몰비는 통상적으로 0.7 내지 1.2이내이다. 공중합체는 경화가능한 알케닐-치환된 폴리오가노실록산 및 공중합체의 합한 중량의 30%이하를 차지하며, 공중합체내 규소 원자의 적어도 한 부위는 치환체로서 비닐과 같은 에틸렌적으로 불포화된 탄화수소 라디칼을 함유한다.Preferred optional components in the compositions of the present invention are resinous organosiloxane copolymers containing triorganosiloxy and SiO 4/2 units. Triorganosiloxy units in this type of copolymer may be represented by the formula R 11 3 SiO 1/2 , wherein R 11 is a monovalent unsubstituted or substituted hydrocarbon radical. In a preferred copolymer, the hydrocarbon radical represented by R 11 is a combination of lower alkyl, most preferably methyl. The molar ratio of triorganosiloxy units to SiO 4/2 units in the copolymer is usually within 0.7 to 1.2. The copolymer accounts for less than 30% of the combined weight of the curable alkenyl-substituted polyorganosiloxane and copolymer, at least one portion of the silicon atoms in the copolymer containing ethylenically unsaturated hydrocarbon radicals such as vinyl as substituents do.
본 발명의 조성물은 상기 조성물의 성분들을 균질하게 배합함으로써 제조한다. 조성물은 성분 (A), (B), (C) 및 (D)가 합해지는 경우에 경화하며 발포되기 시작한다. 조성물이 경화되기 전에 저장하는 것이 바람직한 경우, 이는 2개 이상의 용기내에서 성분들을 별도의 용기내의 오가노하이드로겐실록산[성분(B)] 및 촉매[성분 (D)]과 함께 포장함으로써 달성할 수 있다. 2개 부분 시스템에 있어서는 성분 (i) 및 성분 (v)를 상이한 부분에서 포장하는 것이 바람직하다.The composition of the present invention is prepared by homogeneously combining the components of the composition. The composition cures and begins to foam when components (A), (B), (C) and (D) are combined. If it is desired to store the composition before it is cured, this can be achieved by packaging the components together with the organohydrogensiloxane [component (B)] and catalyst [component (D)] in two or more containers. have. In a two part system, it is preferred to pack component (i) and component (v) in different parts.
경화 및 발포 반응 모두는 경화가능한 조성물을 가열함에 의해 가속화된다. 30 내지 75℃의 반응 온도가 바람직하다. 본 발명의 조성물의 발포 및 경화에 요구되는 시간은 통상적으로 성분의 반응성 및 온도를 기준으로하여, 3 내지 30분이다.Both curing and foaming reactions are accelerated by heating the curable composition. Preference is given to reaction temperatures of 30 to 75 ° C. The time required for the foaming and curing of the composition of the present invention is typically 3 to 30 minutes, based on the reactivity and temperature of the components.
하기 실시예는 본 발명의 조성물의 바람직한 양태를 기술한 것이나 첨부된 특허청구의 범위내에 정의된 본 발명의 영역을 한정하는 것으로 해석되어서는 안된다. 실시예에서 모든 부 및 퍼센트는 중량기준이고 점도는 25℃에서 측정한다.The following examples describe preferred embodiments of the compositions of the invention but are not to be construed as limiting the scope of the invention as defined in the appended claims. In the examples all parts and percentages are by weight and the viscosity is measured at 25 ° C.
실시예 및 비교 실시예의 조성물은 다음과 같이 제조한다. 비교 실시예 A부분은 디메틸비닐실록시-종결된 디메틸실록산의 부위, 수화알루미나 및 피마자 오일을 혼합물의 온도가 150。F에 이를때까지 혼합하여 제조한다. 나머지 디메틸비닐실록시-종결된 디메틸실록산을 혼합하고 이 혼합물을 냉각한다. 다음 나머지 성분을 혼합하고 수득되는 조성물을 진공하에 혼합한다. 비교 실시예 1의 B 부분은 B부분의 성분들의 1/3을 혼합물의 온도가 150。F에 이를때까지 혼합하고, 혼합물의 온도가 100℃ 이하로 강하될 때 나머지 성분을 혼합하여 제조한다.The compositions of Examples and Comparative Examples are prepared as follows. Part A of Comparative Example A was prepared by mixing a portion of dimethylvinylsiloxy-terminated dimethylsiloxane, hydrated alumina and castor oil until the temperature of the mixture reached 150 ° F. The remaining dimethylvinylsiloxy-terminated dimethylsiloxanes are mixed and the mixture is cooled. The remaining ingredients are then mixed and the resulting composition is mixed under vacuum. Part B of Comparative Example 1 was prepared by mixing one third of the components of the B part until the temperature of the mixture reached 150 ° F. and mixing the remaining components when the temperature of the mixture dropped below 100 ° C.
실시예 1Example 1
비교 실시예 1 및 실시예 1 내지 9의 접착 특성을 다음의 방법에 따라 평가한다. 각각의 실시예의 A부분은 A부분의 나열한 성분들을 균질하게 혼합함에 의해 제조한다. 각각의 실시예의 B 부분은 B 부분의 성분들을 균질하게 혼합함으로써 제조한다. A 부분 50부 및 B 부분 50부를 1분간 혼합한다. 혼합물의 박층(대략 3g)을 검정색의 아크릴로니트릴-부타디엔-스티렌 공중합체 플라스틱의 시이트상에 펼쳐놓는다. 플라스틱의 시이트는 1.25 인치 x 6인치 x 0.125 인치(3.18cm x 15.24cm x 0.32cm)로 측정된다. 1인치 x 16인치(2.54cm x 40.64cm)로 측정되고 메쉬 크기가 15인 체를 층위에 두고 가압한다. 혼합물의 다른 3g을 체의 상부에 펼쳐놓는다. 이 혼합물은 발포하기 시작한다. 플라스틱, 체 및 발포체를 오븐내에서 75℃로 10분간 둔다. 플라스틱, 체 및 발포체를 오븐으로부터 제거하고 주위 온도에서 12시간동안 냉각시킨다. 플라스틱 및 발포체를 1인치(2.54cm)의 너비로 트리밍한다. 체의 가장자리를 플라스틱 및 발포체로부터 90도의 각도에서 들어올린다. 발포체 및 플라스틱의 연결부에서 발포체 및 플라스틱의 1인치(2.54cm) 너비를 따라 발포체내에서 절개한다. 체의 가장자리를 장력계내로 클램프하여 박피 강도를 측정한다. 장력계를 1인치(25mm)의 이동 거리, 분당 0.5인치(12.7mm)의 인취 속도 및 100뉴톤의 인취력으로 설정한다. 박피 강도를 표 1에 기록한다.The adhesive properties of Comparative Example 1 and Examples 1 to 9 were evaluated according to the following method. Part A of each example is prepared by homogeneously mixing the components listed in Part A. Part B of each example is made by homogeneously mixing the components of part B. 50 parts A and 50 parts B are mixed for 1 minute. A thin layer (approximately 3 g) of the mixture is spread over a sheet of black acrylonitrile-butadiene-styrene copolymer plastic. Sheets of plastic are measured 1.25 inches x 6 inches x 0.125 inches (3.18 cm x 15.24 cm x 0.32 cm). Pressurize with a sieve measuring 1 inch x 16 inch (2.54 cm x 40.64 cm) and a mesh size of 15 on the bed. Spread another 3 g of the mixture on top of the sieve. This mixture begins to foam. The plastics, sieves and foams are placed in an oven at 75 ° C. for 10 minutes. The plastic, sieve and foam are removed from the oven and cooled at ambient temperature for 12 hours. The plastic and foam are trimmed to a width of 1 inch (2.54 cm). The edge of the sieve is lifted at an angle of 90 degrees from the plastic and the foam. Incisions in the foam and plastic are made in the foam along the 1 inch (2.54 cm) width of the foam and plastic. The edge of the sieve is clamped into a tension gauge to measure the peel strength. The tension meter is set to a travel distance of 1 inch (25 mm), a pulling speed of 0.5 inch (12.7 mm) per minute, and a pulling force of 100 newtons. The peel strength is reported in Table 1.
실시예 2Example 2
비교 실시예 1, 2 및 3과 실시예 10의 접착 특성을 다음 방법에 따라 평가한다. 0.5인치(1.27cm) 너비의 비드 그로브(bead grove)를 갖는 테플론(TeflonR) 주형을 회색의 아크릴로니트릴-부타디엔-스티렌 공중합체 플라스틱의 시이트에 클램프한다. TEFLON은 델라모어주 윌밍톤 거주의 이. 아이. 듀퐁 드 네모아 앤드 캄파니, 인코포레이티드(E. I. DuPont de Nemours and Company, Inc.)의 등록 상표이다. A 부분 50부 및 B 부분 50부를 컵내에서 1분간 함께 혼합한다. 이 혼합물을 혼합물이 주형의 상부의 수준으로 될 때까지 그로브내로 붓는다. 이 혼합물을 발포되도록 한다. 발포체를 경화시키기 위하여 플라스틱 시이트, 테플론 주형 및 발포체를 오븐내에 10분동안 75℃로 둔다. 경화된 발포체를 10분동안 주위 온도로 냉각되도록 한다. 다음 테플론 주형을 제거하여 발포체와 플라스틱 시이트를 제거한다. 플라스틱 시이트에 대한 발포체의 접착을 손으로 시험하여 접착 불량도를 측정한다. 0%의 응집 불량을 나타내는 발포체를 1로 하며, 이는 약한 접착을 나타낸다. 10%이하의 응집 불량을 나타내는 발포체를 2로 하며, 이는 약에서 중정도의 접착을 나타낸다. 10 내지 50%의 응집 불량을 나타내는 발포체를 3으로 하며, 이는 중정도의 접착을 나타낸다. 50%이상 100% 미만의 응집 불량을 나타내는 발포체를 4로 하며, 이는 중정도 내지 강한 접착을 나타낸다. 100% 응집 불량을 나타내는 발포체를 5로 하며, 이는 강합 접착을 나타낸다. 발포체의 접착 특성을 표 2에 나타낸다.The adhesive properties of Comparative Examples 1, 2 and 3 and Example 10 were evaluated according to the following method. A Teflon R template with a 0.5 inch (1.27 cm) wide bead grove is clamped to a sheet of gray acrylonitrile-butadiene-styrene copolymer plastic. TEFLON is a resident of Wilmington, Delamore. children. DuPont de Nemours and Company, Inc., is a registered trademark of EI DuPont de Nemours and Company, Inc. 50 parts A and 50 parts B are mixed together in the cup for 1 minute. This mixture is poured into the grove until the mixture is at the level of the top of the mold. This mixture is allowed to foam. The plastic sheet, Teflon mold and foam are left in the oven at 75 ° C. for 10 minutes to cure the foam. Allow the cured foam to cool to ambient temperature for 10 minutes. The teflon mold is then removed to remove the foam and plastic sheet. The adhesion of the foam to the plastic sheet is tested by hand to determine the degree of adhesion failure. A foam that exhibits 0% agglomeration failure is 1, which shows weak adhesion. A foam exhibiting a cohesive failure of less than 10% is 2, which shows a moderate to moderate adhesion. A foam showing 10 to 50% poor cohesion is 3, which indicates moderate adhesion. A foam having a cohesive failure of at least 50% and less than 100% is 4, which shows moderate to strong adhesion. A foam that exhibits 100% poor cohesion is set at 5, indicating tight adhesion. The adhesive properties of the foams are shown in Table 2.
비교 실시예 1Comparative Example 1
A 부분A part
점도가 25℃에서 55Pa·s인 디메틸비닐실록시-종결된 폴리메틸실록산 72중량% 및 트리메틸실록시와 디메틸비닐실록시로 이루어진 트리오가노실록시 단위 및 SiO2단위(여기서, 트리오가노실록시 단위의 몰비는 SiO2단위의 몰당 0.7몰이다)를 함유하는 수지성 벤젠-가용성 공중합체(여기서, 공중합체는 규소-결합된 비닐 라디칼 1.8중량%를 함유한다) 28중량%로 필수적으로 이루어진 혼합물 75.8중량부.72% by weight of dimethylvinylsiloxy-terminated polymethylsiloxane having a viscosity of 55 Pa · s at 25 ° C. and triorganosiloxy units consisting of trimethylsiloxy and dimethylvinylsiloxy and SiO 2 units (where triorganosiloxy units Is a mixture consisting essentially of 28% by weight of a resinous benzene-soluble copolymer containing 0.7% by mole of SiO 2 units, wherein the copolymer contains 1.8% by weight of silicon-bonded vinyl radicals. 75.8 Parts by weight.
수소화된 피마자 오일 1중량부.1 part by weight of hydrogenated castor oil.
탄소 블랙 0.5중량부.0.5 parts by weight of carbon black.
수화알루미나 14.8중량부.14.8 parts by weight of hydrated alumina.
벤질 알콜 7.2중량부.Benzyl alcohol 7.2 parts by weight.
백금 0.65중량%를 제공하기 위해 디메틸비닐실록시 말단차단된 폴리디메틸실록산으로 희석된 디비닐테트라메틸디실록산의 클로로플라틴산 착체 0.53중량부.0.53 parts by weight of chloroplatinic acid complex of divinyltetramethyldisiloxane diluted with dimethylvinylsiloxy terminated polydimethylsiloxane to provide 0.65% platinum.
B 부분Part B
점도가 25℃에서 55Pa·s인 디메틸비닐실록시-종결된 폴리디메틸실록산 72중량% 및 트리메틸실록시와 디메틸비닐실록시로 이루어진 트리오가노실록시 단위 및 SiO2단위(여기서, 트리오가노실록시 단위의 몰비는 SiO2단위의 몰당 0.7몰이다)를 함유하는 수지성 벤젠-가용성 공중합체(여기서, 공중합체는 규소-결합된 비닐 라디칼 1.8중량%를 함유한다) 28중량%로 필수적으로 이루어진 혼합물 55.5중량부.72% by weight of dimethylvinylsiloxy-terminated polydimethylsiloxane having a viscosity of 55 Pa · s at 25 ° C. and triorganosiloxy units consisting of trimethylsiloxy and dimethylvinylsiloxy and SiO 2 units (where triorganosiloxy units Is a mixture consisting essentially of 28% by weight of a resinous benzene-soluble copolymer containing 0.7% by mole of SiO 2 units, wherein the copolymer contains 1.8% by weight of silicon-bonded vinyl radicals. Parts by weight.
수소화된 피마자 오일 2중량부.2 parts by weight of hydrogenated castor oil.
통상적인 입자 크기가 5마이크론 미만인 석영 25.8중량부.25.8 parts by weight of quartz having a typical particle size of less than 5 microns.
필수적으로 대략 0.75 : 1 의 몰비의 (CH3)3SiO1/2단위 및 SiO2단위로 이루어지고 FTIR(ASTM E-168)에 의해 측정된 것으로써 고체를 기준으로 하이드록실 약 2.65중량%를 함유하는 실록산 수지 공중합체의 70중량%의 크실렌 용액 58.8중량%와 점도가 0.13 Pa·s이고 규소-결합된 수소 원자의 함량이 1.6중량%인 트리메틸실록시 말단차단된 폴리메틸하이드로겐실록산 41.2중량%를 배합시킨후 가열하여 실질적으로 모든 용매를 제거함으로써 수득한 생성물 12.3중량부. 이 생성물의 점도는 약 1400mm2/s이고, SiH의 함량은 약 0.8중량%이며, 하이드록실 함량은 약 1.7중량%이다.Essentially approximately 2.65% by weight of hydroxyl, based on solids, consisting of (CH 3 ) 3 SiO 1/2 units and SiO 2 units in a molar ratio of approximately 0.75: 1, measured by FTIR (ASTM E-168). 41.2 weight of trimethylsiloxy-terminated polymethylhydrogensiloxane having a viscosity of 0.13 Pa.s and a content of silicon-bonded hydrogen atoms of 1.6% by weight of 58.8% by weight of a 70% by weight xylene solution of the siloxane resin copolymer 12.3 parts by weight of product obtained by combining% with heating to remove substantially all solvent. The viscosity of this product is about 1400 mm 2 / s, the content of SiH is about 0.8% by weight, and the hydroxyl content is about 1.7% by weight.
분자당 평균 5개의 메틸하이드로겐실록산 단위 및 3개의 디메틸실록산 단위를 가지며 규소-결합된 수소 원자의 함량이 0.8중량%인 트리메틸실록시-종결된 폴리디오가노실록산 4.6중량부.4.6 parts by weight of trimethylsiloxy-terminated polydiorganosiloxane having an average of 5 methylhydrogensiloxane units and 3 dimethylsiloxane units per molecule and 0.8% by weight of silicon-bonded hydrogen atoms.
비교 실시예 2Comparative Example 2
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
백금 0.65중량%를 제공하기 위해 디메틸비닐실록시 말단차단된 폴리디메틸실록산으로 희석시킨 디비닐테트라메틸디실록산의 클로로플라틴산 착체 1.5중량부.1.5 parts by weight of chloroplatinic acid complex of divinyltetramethyldisiloxane diluted with dimethylvinylsiloxy terminated polydimethylsiloxane to provide 0.65% platinum.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.8중량부.0.8 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight of vinyl radicals and 8% by weight of hydroxyl groups.
γ-글리시드록시프로필트리메톡시실란 1.2중량부.1.2 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
알루미늄 아세틸아세토네이트 0.05중량부.0.05 parts by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
비교 실시예 3Comparative Example 3
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
백금 0.65중량%를 제공하기 위해 디메틸비닐실록시 말단차단된 폴리디메틸실록산으로 희석시킨 디비닐테트라메틸디실록산의 클로로플라틴산 착체 1중량부.1 part by weight of chloroplatinic acid complex of divinyltetramethyldisiloxane diluted with dimethylvinylsiloxy endblocked polydimethylsiloxane to provide 0.65% platinum.
γ-글리시드록시프로필트리메톡시실란 1.26중량부.1.26 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.51중량부.0.51 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.11중량부.0.11 part by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.05중량부.0.05 parts by weight of aluminum acetylacetonate.
실시예 1Example 1
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.13중량부.0.13 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.5중량부.0.5 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.25중량부.1.25 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
테트라에틸오르토실리케이트 0.5중량부.0.5 parts by weight of tetraethylorthosilicate.
실시예 2Example 2
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.5중량부.0.5 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.1중량부.0.1 part by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.05중량부.0.05 parts by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.25중량부.1.25 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
테트라에틸오르토실리케이트 0.5중량부.0.5 parts by weight of tetraethylorthosilicate.
실시예 3Example 3
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.5중량부.0.5 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.5중량부.0.5 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.5중량부.1.5 parts by weight of γ-glycidoxypropyltrimethoxysilane.
테트라에틸오르토실리케이트 1.5중량부.1.5 parts by weight of tetraethylorthosilicate.
실시예 4Example 4
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.25중량부.0.25 parts by weight of a hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight of vinyl radicals and 8% by weight of hydroxyl groups.
테트라부틸티타네이트 0.5중량부.0.5 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.5중량부.1.5 parts by weight of γ-glycidoxypropyltrimethoxysilane.
테트라에틸오르토실리케이트 1.5중량부.1.5 parts by weight of tetraethylorthosilicate.
실시예 5Example 5
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.13중량부.0.13 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.5중량부.0.5 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.5중량부.1.5 parts by weight of γ-glycidoxypropyltrimethoxysilane.
테트라에틸오르토실리케이트 1.5중량부.1.5 parts by weight of tetraethylorthosilicate.
실시예 6Example 6
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.13중량부.0.13 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.1중량부.0.1 part by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.05중량부.0.05 parts by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 0.6중량부.0.6 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
테트라에틸오르토실리케이트 0.5중량부.0.5 parts by weight of tetraethylorthosilicate.
실시예 7Example 7
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.15중량부.0.15 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.1중량부.0.1 part by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 0.25중량부.0.25 parts by weight of γ-glycidoxypropyltrimethoxysilane.
테트라에틸오르토실리케이트 1중량부.1 part by weight of tetraethylorthosilicate.
실시예 8Example 8
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.32중량부.0.32 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.3중량부.0.3 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.05중량부.1.05 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
테트라에틸오르토실리케이트 1중량부.1 part by weight of tetraethylorthosilicate.
실시예 9Example 9
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.13중량부.0.13 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.25중량부.0.25 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.25중량부.1.25 weight part of (gamma)-glycidoxy propyl trimethoxysilane.
테트라에틸오르토실리케이트 1중량부.1 part by weight of tetraethylorthosilicate.
실시예 10Example 10
A 부분A part
비교 실시예 1의 A 부분 50중량부.50 parts by weight of the A portion of Comparative Example 1.
비닐 라디칼 10.5중량% 및 하이드록실 그룹 8중량%를 함유하는 하이드록실-종결된 디메틸실록산/메틸비닐실록산 공중합체 0.5중량부.0.5 parts by weight of hydroxyl-terminated dimethylsiloxane / methylvinylsiloxane copolymer containing 10.5% by weight vinyl radical and 8% by weight hydroxyl group.
테트라부틸티타네이트 0.5중량부.0.5 parts by weight of tetrabutyl titanate.
알루미늄 아세틸아세토네이트 0.1중량부.0.1 part by weight of aluminum acetylacetonate.
B 부분Part B
비교 실시예 1의 B 부분 50중량부.50 parts by weight of part B of Comparative Example 1.
γ-글리시드록시프로필트리메톡시실란 1.5중량부.1.5 parts by weight of γ-glycidoxypropyltrimethoxysilane.
테트라에틸오르토실리케이트 1.5중량부.1.5 parts by weight of tetraethylorthosilicate.
본 발명에 의해 경화시, 플라스틱을 포함하는 각종 기판에 대한 접착성이 향상된 실리콘 발포체를 생성하는 발포성의, 경화가능한 오가노실록산 조성물이 제공된다.The present invention provides a foamable, curable organosiloxane composition that, upon curing, produces silicone foams with improved adhesion to various substrates, including plastics.
Claims (3)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/775,123 | 1996-12-30 | ||
| US08/775,123 US5683527A (en) | 1996-12-30 | 1996-12-30 | Foamable organosiloxane compositions curable to silicone foams having improved adhesion |
| US8/775,123 | 1996-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR19980064777A true KR19980064777A (en) | 1998-10-07 |
| KR100580799B1 KR100580799B1 (en) | 2006-09-28 |
Family
ID=25103396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970076170A KR100580799B1 (en) | 1996-12-30 | 1997-12-29 | Foamable organosiloxane compositions curable with silicone foams with improved adhesion |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5683527A (en) |
| EP (1) | EP0851002B1 (en) |
| JP (1) | JP4018219B2 (en) |
| KR (1) | KR100580799B1 (en) |
| AU (1) | AU726202B2 (en) |
| DE (1) | DE69703021T2 (en) |
| TW (1) | TW455624B (en) |
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| KR20190023103A (en) * | 2016-07-13 | 2019-03-07 | 다우 실리콘즈 코포레이션 | Formulation containing a metal aprotic organic silane oxide compound |
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- 1996-12-30 US US08/775,123 patent/US5683527A/en not_active Expired - Lifetime
-
1997
- 1997-05-01 US US08/846,446 patent/US5744507A/en not_active Expired - Lifetime
- 1997-12-15 TW TW086118915A patent/TW455624B/en not_active IP Right Cessation
- 1997-12-18 EP EP97122354A patent/EP0851002B1/en not_active Expired - Lifetime
- 1997-12-18 DE DE69703021T patent/DE69703021T2/en not_active Expired - Lifetime
- 1997-12-24 AU AU49259/97A patent/AU726202B2/en not_active Ceased
- 1997-12-29 KR KR1019970076170A patent/KR100580799B1/en not_active IP Right Cessation
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1998
- 1998-01-05 JP JP00040298A patent/JP4018219B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120106744A (en) * | 2009-11-09 | 2012-09-26 | 다우 코닝 코포레이션 | Process for preparing clustered functional polyorganosiloxanes, and methods for their use |
| KR20190023103A (en) * | 2016-07-13 | 2019-03-07 | 다우 실리콘즈 코포레이션 | Formulation containing a metal aprotic organic silane oxide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0851002B1 (en) | 2000-09-06 |
| JPH10195217A (en) | 1998-07-28 |
| AU4925997A (en) | 1998-07-02 |
| DE69703021T2 (en) | 2001-05-03 |
| TW455624B (en) | 2001-09-21 |
| DE69703021D1 (en) | 2000-10-12 |
| AU726202B2 (en) | 2000-11-02 |
| KR100580799B1 (en) | 2006-09-28 |
| EP0851002A3 (en) | 1998-11-11 |
| US5683527A (en) | 1997-11-04 |
| JP4018219B2 (en) | 2007-12-05 |
| EP0851002A2 (en) | 1998-07-01 |
| US5744507A (en) | 1998-04-28 |
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